Dolly Mae

After I decided to divorce my wife, I left her and rented a room from a lady in town. I was still walking for exercise and explored my new neighborhood for a safe place to walk in the mornings.

The next day I started walking in the area I had explored previously. I knew there was a little park close by so I made my way there taking the long way around. I approached a house on the corner and saw a lady under the carport. I couldn't see much of her with the shade but I was able to see her silhouette.

She appeared to be short and a little fluffy. I would not call her skinny but would not say fat either. I'll say she was petite in statue and rounded. As I turned the corner, I could see her better. She had short dark grey hair. Her hair wasn't straight, but it wasn't really curly either. I supposed wavey would be a good way to describe it.

She wasn't the prettiest lady but I found her to be desirable. She had on a night gown and I could see the shape of her naked body from the sun shining across the carport. I could tell she had granny panties on but she had nothing else on under the gown.

When I got home, I questioned who she was with my landlord. I didn't want to make it obvious that I found her interesting. She told me her name was Dolly and continued by saying he was not a very friendly lady.

From then on, I paid attention to her house when I passed in my truck or while walking. I saw she had a husband but he didn't look too healthy. I searched her on the internet and found out she was in her early 80's.

After a few months, I started getting her attention while I passed by. If I saw her outside, I would always greet her in some way. Sometimes on my walk, we would get into a small conversation about the weather or current events. It was always the highlight of my walk. She was the one who kept up the property and the property across the street where her daughter lived. Once a week you would see her cutting the grass on a riding lawn mower. She would also use a weed eater to trim the areas around the house.

A couple years had passed, and I learned her husband had passed away. It didn't seem to have much of an effect on her. She continued her normal life. She continued cutting the grass and doing her weekly grocery shopping. Sometimes I would see her at the grocery store and have a short visit with her. I tried to pay attention to what type of groceries she would buy so I could learn a little more about her. I was curious if she ever bought any panty liners or feminine products you often see older ladies buy.

I could tell she was getting more comfortable with me. I can see why my landlord said she was not too friendly but I was able to get on her good side. Eventually, while I walked, she would meet me outside and offer me a bottle of water. Sometimes she would invite me inside to drink my water or we would sit outside under her patio. Dolly became a little more friendly each time we would visit. I particularly liked when I would see her outside in her gown or house dress.

Sometimes, when the sunlight was shining just right, I would see right through her gown. Sometimes I could see she wore panties and sometimes I could tell she didn't have panties on. I could see her figure perfectly in the light. Her breasts did sag some as you would expect on a lady her age but they did look full and larger than average. If I had to guess, I would say she wore a 38D bra. Again, if I had to guess the size of her panties, I would guess a size 6-7.

Dolly had shapely legs. I mean her legs might have been thick but you could see she had ankles, calves, knees and thighs. I would get turned on seeing her like that. Often, I would fantasize of her being nude. You could tell she was not a 20-year-old. Her body showed signs of being a matured lady but she looked wonderful.

Eventually, I would give her a hug and then later a kiss. My visits during my walks would be longer each time. I was getting to know her pretty well and I found her to be an interesting lady. Once you got to know her and where she came from in life, there was so much to like. I was starting to understand her and why someone might say she wasn't friendly.

She had rough marriage but didn't have the means to get out of it. She would describe it as a "loveless" marriage. She never felt her husband really loved her or just didn't know how to show it. She never felt sex was fulfilling. As she described it, she said she always felt something was missing. She never understood why some people liked it so much when it often felt like it wasn't worth the trouble.

The talks about her marriage and sex life were more detailed at times. I tried to describe what sex should be like. I told her that a married couple or people who love each other should make love not just have sex. She asked me to describe the difference as he didn't know there was a difference. I told her that my marriage was the same except my ex-wife didn't know there was as difference. I continued by telling her that having sex is just that; intercourse. To have sex with a person doesn't mean you have feelings for that person. Basically, it just to release sexual frustrations. Which nothing is wrong with it.

Often married couples will have sex even if they usually make love. I went on by telling her that making love is so much more personal. It's when you care for each other enough to satisfy the other person above your own satisfaction. It's when you explore each other's bodies and do what it takes to make that person feel like they are the most important person on earth.

She asked if only married couples made love or could two people who aren't married make love. I said any two people can make love. You don't have to be married to make love. You cannot be selfish of your own feelings. You have to care enough for that person to want to satisfy and fulfill their needs above your own needs. I told her that sometimes sex is fulfilling and satisfying without making love. She said that it could get confusing. I agreed but also told her that she will know the difference once she makes love.

With that, she reached and kissed me on my lips and said she likes how I make her feel. She felt I made her feel special. Her daughter arrived at her house about that time and we had to end that conversation. It was time for me to continue my walk and we would finish that topic another time.

For the rest of my walk and the next few days, I couldn't get Dolly off my mind. I knew her situation was normal for her generation. Many older couples just didn't know any different because sex was not openly discussed how it is now. Most couples her age only new one sexual position. Oral sex was not even in their imagination much less an option when they were in bed.

I fantasized of undressing her and performing oral sex on her. I thought of how she would enjoy it so much the intimacy if I ever had the chance. I wondered how she would react if I ever had the chance to explore her body and get the chance to satisfy and fulfil her every need. I definitely wanted to continue that last conversation with her. I had many questions that I wanted answered but I didn't want to come out and ask the questions directly. I had to be sneaky with it because I didn't want to scare her away. She seemed to have interest in me and I wanted to keep it that way.

We continued to visit when I walked or saw her in town. Every time we talked, we got more comfortable with each other. We learned more about each other and she learned that I use to be an appliance technician for Sears.

One day I ran into Dolly at the grocery store and she told me her washing machine was acting different and asked me if I could have a look at it for her. I suggested the next day would be good for me and she agreed. We made plans for me to go there for 8:00am. She seemed happy that I was going and I was excited to have plans with her. I knew she would be alone because I had gotten to know her schedule the last few years.

People are creatures of habits and usually keep the same schedule unless something unexpectedly changes. Dolly and her family seemed to always keep the same schedule. I also knew at that time of the morning; Dolly is usually still in her night gown. My mind raced all night in anticipation of what would happen on this visit. I wondered if her washing machine was really acting up or was, she just wanting me to go visit. It didn't matter to me; I was excited to visit her at home.

I woke up the next morning very excited to go see Dolly Mae. In fact, I woke up with an erection anticipating the visit. I would normally take care of that when I showered but this time, I didn't want to so I could make sure I was ready for Dolly if anything sexual were to happen. I had a feeling that nothing was really wrong with her washing machine.

I showered, dressed, grabbed my tool bag and drove to Dolly's house. When I arrived, I noticed the door was closed. I hoped I had not misunderstood the day or time I was to be there. I rang the doorbell and Dolly opened the door. It was obvious she was waiting for me and took some time to prepare for my arrival. She had put on a little make up and styled her hair. She was a wearing a knee length night gown and slippers. She closed the door behind me and gave me a kiss and a hug. The kiss was on the lips but more like a mother/grandmother kiss. I looked at her in the eyes and kissed her again.

This time I held my lips to hers. I knew I would have to teach her to kiss passionately. I know she felt the passion but didn't know how to show it. While kissing her, I passed my hand over her back side and noticed she didn't have any panties on. It didn't take Dolly long to learn to let her feelings out through her kisses and caressing. She learned quickly how to kiss passionately. The more I would caress her body, the more she would let her feelings out.

I then told her that I better look at her washing machine before I forget while I was really here. She said the washing machine started working properly when she tried it again. I suspect it was just an unbalanced load because she said she washed 2 batches of clothes after she talked with me.

We then walked to the den and sat on the couch. I walked behind her so I could see her back side shimmy as she walked ahead of me. The more I got to know Dolly, the more interested I was in her. She told me she never felt so comfortable with sex before. She said her husband never made her feel so comfortable and relaxed.

Our kisses started getting better as the minutes passed. She was letting her natural desires flow. I repositioned myself where I was kneeling on the floor and had her lying on the couch. We sort of just moved into that position, it wasn't planned or anything. Things were moving a lot faster than I anticipated. I wanted to give her pleasures she never had before and I knew it would be difficult on the couch.

While kissing Dolly, I was caressing her body everywhere I could reach. I suggested we go to the bed room to be more comfortable. Dolly agreed with my suggestion however she admitted she was nervous. She told me she had only been with one man and that her experiences were nothing like what I had described previously. I told her not to worry and just let nature take over. I assured her that everything would be fine. I also assured her that at any time she wants to stop, just let me know. She said she trusted me and was not concerned with that.

I stood up and helped Dolly up off the couch. I hugged and kissed her again and followed her to down the hall to the bed room. As we walked down the hall, I watched her walk from behind and I removed my shirt.

When we entered the room, I quietly removed my shorts too. When Dolly turned around, she was surprised to see I had removed my clothes. I kissed her and lifted her gown over her head. It was the first time I saw her body without any clothes on. I was very amazed at how nicely she had kept herself looking. Her skin was soft and smooth. Her breast was sagging but full and rounded. Her nipples were larger than expected but still on the smaller side and a dark pink in color. She had a nice rounded rear side and a fluffy belly. She was a very appealing matured lady. I couldn't wait for her reaction when I was to stat exploring her body with my hands, lips and tongue.

The anticipation of tasting her vagina was getting the best of me. I sat her on the edge of the bed and kissed her lips again. She wrapped her arms around me and let her passion take over the moment. I took her right breast in my left hand and gently caressed it. She let out a quiet little moan and her kisses got more intense. I don't think she even had the chance to let the passion take over like this in all of her years. It all seemed so new to her. I moved my kisses from her lips to her neck and ears. She was enjoying the pleasures.

I then kissed her breasts. She went to a lying down position on the edge of the bed and I was admiring her body with my hands and lips. I explored every inch of her matured body. My hands reached her legs and I felt her body stiffen a little. I continued kissing her legs until I felt her relax some.

I rubbed her feet and she let me know how good it felt. She said no one has ever rubbed her feet before and she really liked how it felt. Her feet were little, probably about a size 5 or 6. They had smooth soft skin so I figured you used lotion on them often. I then kissed her feet as my hands caressed her ankles. I moved my caresses up her legs to her ankles and then her knees followed by kisses.

When I reached her inner thighs, she tried to cover her pubic mound with her hand. I pretended not to see it and just kissed around the hand. After a few minutes, she relaxed and moved her hand. I hurried and kissed her vaginal lips before she covered it again. I heard her take a deep breath as my lips touched her vagina lips.

I could tell she was embarrassed since she never had that done before but I continued before she had a chance to stop me. She tasted so clean and pure. I could smell her womanly scent. She smelled so natural. I separated her vaginal lips with my tongue.

Dolly shifted her position a little but did not try to stop me anymore. Her Pubic mound had very little hair on it. The little hair that was there was a little lighter than the color of her hair on her head. I found it to be very sexy. I didn't want to stop licking her vagina because it was so good. Dolly stated tensing her legs and her breathing got heavy when I all of a sudden, with out warning, felt her orgasm. She begged me to stop as he never had felt anything like that before. It appeared she was afraid.

I was able to get her to lie in the bed and I cuddle in besides her. She told me that she never felt that before. She said it felt really good but it scared her because her chest was beating heavy. I told her that she had an orgasm and asked if she never had an orgasm before. She told me no, nothing like that. She said she really never enjoyed sex. She said when she got married, neither her or her husband knew anything about sex. It was often painful for her.

They had sex usually only when he wanted to do it. She continued by saying she ever felt like this before where she wanted to have sex. She would really like to know how it felt with a man that cared like I do. She admitted to having a feeling inside her body that she never felt before. She wanted my erection inside of her but didn't want to disappoint me. I told her she would not disappoint me and that I understood her situation.

I then starting kissing her lips again passionately. I caressed her breasts and she moaned quietly. I then took her hand and placed it on my erection while I continued kissing her lips.

While she was holding my erection, I cupped my hand over her pubic area. I gently rubbed a little and slipped a finger inside of her vagina. She was still very wet so I thought it would be a good time to penetrate her. I positioned myself on top of Dolly. I placed her feet over my shoulders and confirmed with her that she was okay. I rubbed my erection on the outside of her vagina to make sure my erection was lubricated with her juices. I gently pushed my erection into her outer lips of her vagina.

It felt very tight and I didn't want to hurt her. I surely didn't want to scare her again. I would push in and wait a bit to make sure she was comfortable with me penetrating her. It was almost like making love to a virgin. I asked if she was okay and she verified she was fine. I told her to please stop me if it hurt or was too uncomfortable. The next push in she said it was uncomfortable. I told her it would be until I went all the way in. I made sure it didn't hurt and it was just uncomfortable to her. She said it didn't hurt that it just felt pressure.

I wanted to get past that point so she would enjoy it more but again, I didn't want to hurt or scare her. I pushed a little harder and got it in enough that the pressure and discomfort disappeared. I felt her relax when I got my erection deeper inside of her. I pulled out a little and developed a smooth steady rhythm with her. She started moaning again and told me how good it felt inside of her. Dolly started thrusting her pelvis to meet my rhythm.

The look on her face was so satisfying. I felt my testicles get tight and the anticipation of my sperm filling up Dolly's vagina was building. Her breathing was getting heavier and I knew it wasn't long before she orgasmed. I wanted to hold off as long as I could so she would be satisfied and fulfilled. I also knew Dolly hasn't really had a good orgasm before so I didn't want it to scare her before I filled her with my cum.

I increased my rhythm to try to get her to orgasm sooner and it worked. Dolly started having an orgasm that lasted longer than expected. Her body started thrusting uncontrollably. Her breathing was heavy and her legs tightened around me.

I then shot my load of cum deep inside of her. I went in and out of her a few times until all my cum was inside of her. Her body went limp and her entire body glowed with satisfaction. I kept my erection inside of her vagina until it went flaccid and fell out on its own.

I got off of Dolly and laid on side of her. She was speechless as I kissed her lips again. Her body was trembling and she was trying to catch her breath. She tried speaking a couple times before being able to say a sentence without losing her breath. Her body would have mini convulsions as she settled down. She finally managed to tell me that she never felt anything so wonderful. She said it scared her at times but she trusted me.

While Dolly was laying in bed settling down, I went to the bathroom and got a warm wet towel. I went back to her side the bed and cleaned her pubic area. She asked me to be gentle was it was sensitive to the touch now. I did notice a little pinkish colored discharge after I wiped her vagina clean. I wasn't alarmed and didn't even mention it to her knowing it had been many years since she had sex and also because she was so tight. I went put the towel in the lavatory for later and returned to the bed.

By this time, Dolly was relaxed and ready to talk and cuddle. She told me how she never experienced such a wonderful feeling before in her life. Sex with her husband was never this intense. She asked if it would be like that every time with me. I told her I hoped it would and it was good to know she considered another time. She said she hoped we could do it on a regular basis but not too soon. She said how she felt sore down there.

I assured her it would be okay and as time passed it would not get sore anymore. I also told her there is much more I would like to introduce to her. She said she couldn't imagine. She continued by telling me how much she enjoyed when I kissed her down there.